tagGroup SexStepmom's Special Day

Stepmom's Special Day


Although she was not technically a mother, Mother's Day was still one of Jillian's favorite days. Her husband always made sure that he and his boys did something special for her to show their appreciation for everything she did for them. She loved the men in her life and was happy to have them all. She thought of her stepsons as her own and knew they saw her as their mom just as much as their real one.

It was rocky going at first. Jillian met her husband when he was in the middle of a tricky divorce and the boys were not happy to see a new woman in their father's life. It was like the last hope of keeping their family together was gone. The only saving grace was that she was so young that she played with them more like a babysitter or a big sister. Jillian met her husband when she was interning at his company during her final year of college. He was twelve years older than her and while it had seemed scandalous at the time, the age difference never meant anything to her. The heart wants what the heart wants. They were married the winter after she graduated and at twenty-three she found herself the stepmother to two boys, ages ten and eight. In the beginning they had the boys on weekends, but then their mother took a job out of town and the boys came to live with them full time. They saw their mother on holidays and for several weeks in the summer, but the day-to-day work of being a mother fell to Jillian. She chafed at the responsibility at first, but soon found her groove. Now, ten years later, they were a happy family.

Jillian rolled over in bed and looked at the clock. It was past ten. Mother's Day was one of the few days she got to sleep in, but usually she was still up before this. But her husband was out of town on business and she thought maybe the boys had forgotten to plan something. They loved her, but they were young guys. Mother's Day was probably not foremost in their minds.

"Hey, are you up yet?" Sam called. He knocked lightly, but then came right through the bedroom door. Although she was laying on top of the sheets in just a stretch cami and panties, she didn't think to cover up. Normally she did not prance around half naked in front of the boys, but she wasn't uptight about it.

"Yeah, I just woke up. It felt great to sleep in." She stretched and then pulled the sheet over her.

"Well, it's time to get up because we have brunch reservations at eleven-thirty. Chop --chop." Sam tried not to let his gaze linger over her body as she stretched and was relieved when she covered up. He leaned forward and handed her the cup of coffee he'd brought.

Seeing his stepmom like that caused a stirring in his pants. How could it not? He was a normal, eighteen-year-old kid and although she was in her mid-thirties he still thought she was hot. Her top clung to her trim body and her nipples poked right through it. It didn't quite meet the striped bikini panties she wore. She and his father were both physically active, running, playing tennis, and were in great shape. Her petite body was in just as great shape as when he'd first met her. Over the years when he'd seen her in a bathing suit or if he accidentally caught her in a state of undress he'd gotten wood and at first he felt really weird about it. He even jerked off a few times thinking about how hot she was. He thought there must be something wrong with him until his older brother, Nick, told him that he felt the same way.

Nick said it was perfectly natural. "Hey, she's as close to our age as she is to Dad's," he said. "It's like having a crush on your babysitter, dude."

It made Sam feel better, but on the few occasions when he jerked off thinking about Jillian over the years he still felt guilty.

"That's sweet. I thought maybe you guys forgot about me this year."

"We'd never do that. Nick made reservations last week."

"Then you'd better get out of here so I can get ready." Jillian's smile was luminous.

As soon as Sam had gone she threw off the covers and jumped in the shower. She got ready as quickly as she could, but she did want to look nice for her boys, so she took time with her shoulder-length auburn hair and applying her make-up. When she came out, the boys were both dressed and waiting. They looked nice, wearing khaki slacks and dress shirts, Sam in blue and Nick in a light green. The boys were half Filipino, their father was born in that country, and the light shirts looked good with the darker skin. Both boys had grown into fine, handsome young men in her opinion.

"I was starting to think you weren't coming out of there," Nick said grinning.

"Didn't your father tell you women are never on time? Hopefully you think we're worth it," Jillian laughed.

"Well, you're certainly worth it. You look beautiful," he replied.

"Thanks honey. You'll have the girls eating out of your hand with that silver tongue of yours." Nick was an inch or two over six feet and even in her high heeled sandals she had to stand up on tip-toes to kiss his cheek. Nick was going to local college and even though he no longer played football, like he had in high school, he was still built like granite. He slipped his arm around her waist and hugged her against him. Feeling his strength, Jillian understood why he never had trouble getting girls.

It was a gorgeous spring day, warm for May, and they sat outside on the patio at a local restaurant. Jillian was seated between her boys and they treated her like a princess, even ordering her French toast with berries for her. They also made sure the mimosas kept flowing. Jillian was not usually much of a drinker, but the mimosas were excellent and she was not paying attention as she sipped them throughout their meal. Feeling warm, she slipped off the pink sweater that matched her snug, sleeveless top. The outfit was not something she thought of as sexy, but it did show off her figure well. Her patterned skirt came to a couple inches above her knees.

The boys were witty and fun and it was great to have the time to catch up on what was going on with their lives. Sam was a senior in high school and had already decided to go to Penn State in the fall. Jillian had had a great time in college and told him she was sure it would be great for him as well. She thought Nick made a mistake by standing home for school. Being away from college was a great time to experiment and figure out who you are. That decision may have been made, but his plans for prom were less concrete. Sam had been having problems with his girlfriend and wasn't sure if they would still be together by then. He didn't want to be left without a date at the last minute.

"I think you and Emma are cute together. What's wrong?" Jillian asked, putting her hand on Sam's.

"I dunno. I think it's just that high school is almost over and we're going to different schools, so Emma doesn't want to get too close. Her friends keep telling her she has to be single for college," Sam said.

"Tell Jill the real reason you're not getting along. Emma won't put out," Nick chuckled.

"Nick, do you have to be so crude?" Jillian asked. "I'm sure that's not it." Her stepsons' sex lives weren't something she thought about, but Sam had been with Emma for almost a year and she just assumed they were doing it. She knew their father gave them The Talk a few years ago.

"If I was dating a chick for that long and she didn't give it up I know I would be looking around too. Hey, little bro is a man now."

"Not all boys are only interested in one thing, Nick," she scolded, although that wasn't quite true in her experience. Their father had gone for it on their second date and she happily gave it up. He was rugged and handsome, an older version of his sons, and she'd wanted him. After so many years of marriage they still had a great sex life and his being across the country working on a project for a month had been hard for her. Phone sex could only make up for so much.

"Well, it is frustrating," Sam admitted. "She's not my first girlfriend, you know. But that's not it. She's just pulling away from me so letting go will be easier."

"I guess I understand that," Jillian said.

"I'm telling you, it's the sex. I bet you can crush walnuts with your right hand," Nick laughed.

"Dude!" Sam complained, turning crimson. Part of his embarrassment was that his brother was right. Emma used her hand on him, but that was about it. At least if she would blow him it would be easier to take. He was on the baseball team and knowing there were plenty of girls who would be more than willing to take Emma's place made her holding out even harder. He just wasn't the alley cat his brother was.

"Nick, give your brother a break. Maybe he doesn't want a different girl every week like you do." It had always bothered her how Nick picked on his little brother. She thought it was sweet that Sam was faithful to his girlfriend.

"But it's so much fun. Besides, when you're our age it's the time to get some experience and learn what chicks like in bed. You've got to be ready when you settle down," Nick said.

"Is that what your father told you?"

"Of course," Nick grinned.

In fact, his father had told Nick about his conquests in great detail. In his day he'd been quite the cocksman and Nick was proud to follow in his father's footsteps. He knew his father loved Jillian, but he also doubted that his father was holding out while he was away for so long. There was no way a man like that could go without for so long. He wondered how Jillian was holding up. One night his dad got really smashed and told him how amazing she was in bed. "When you get to be my age you've got to find yourself a hot, younger woman, son," he'd said. There were a few times over the years, when they thought he and Sam were asleep, that Nick had overheard just how much fun his father and stepmother were having. Like his brother, he'd beaten off more than once thinking about his sexy, young stepmom.

"Well, I don't want to contradict your father, but I'm sure he didn't mean you should go through women like tissues. He was just trying to tell you that it's important to sow your oats before you settle down."

"Yeah, I'm sure that's what he meant," Nick said sarcastically.

"So you're just getting all this experience for the benefit of your future wife?"

"Yeah. I want to make sure I can take care of all her needs."

"And how is that working out for you? Do you think you know what you're doing yet?" She couldn't believe she was talking about sex so frankly with her stepsons, but the mimosas were flowing and they were having fun, so she wasn't thinking too clearly.

"I haven't had any complaints yet. I think I know what I'm doing. Don't you want a man who knows what he's doing in bed?"

It was her turn to blush. "I, uh, yeah, I guess. It's important. Your Dad keeps me happy."

"I'm sure," Nick said knowingly.

Jillian was ready to change the subject. Talking about her husband only made her remember how much she missed him being in their bed. "Don't listen to your brother," she told Sam. "It's about quality, not quantity."

"Don't worry, I know what I'm doing. I think some things come naturally," Sam said. He was shocked by the turn in their conversion too, but thought it was kind of hot to hear Jillian talking about sex. "So which would you rather have? A guy who's been with a lot of girls, or someone who's always been faithful?"

"I want my man to be faithful to me, but I want him knowing what he's doing. I guess I don't care how he knows," Jillian laughed. The more they talked about sex the easier it became.

"So is Dad the best you've had?" Sam asked.

"That's a personal question."

"Yeah, but is he?" Nick chimed in.

She squirmed in her seat, knowing she should change the subject, but she was feeling naughty, so she smiled and said, "Your father is very, very good. You should listen to anything he tells you."

"Do you have a lot to compare him to?" Nick asked.

"Look, here comes the flower girl," she dodged.

A pretty blonde, about the boys' age, came around with a basket of roses and the boys each bought her one. Jillian was touched and gave each of them a hug and a kiss. Nick held her for a moment longer than his brother and instead of offering his cheek he kissed her on the lips. It wasn't a lover's kiss, but it left Jillian feeling flushed after what they'd been talking about.

They drained the last of their drinks and got up to head home. Jillian really felt all those mimosas then and leaned against Sam for support. He was nearly as big as his brother and easily held her lithe body. His hand rested on her hip and she pressed against him as they walked out to the car. They could have almost been mistaken for a couple. When he helped her into the car, she was careful to smooth her skirt over her lap, so as not to flash too much leg. All their sex talk had her feeling self conscious.

When they returned home the boys asked how she wanted to spend the rest of the day. Feeling tipsy, Jillian just wanted to lay back and chill out on the couch, maybe watch her favorite movie, Titanic. She didn't get a chance to sit and watch the long movie all the way through very often. She was surprised when the boys said they would watch it with her and rather than letting her go slip into something more comfortable, Nick guided her to the big couch in the family room, while Sam put the DVD on and drew the curtains. Although it was mid afternoon, only a filmy light came in through the curtains, dimming the room enough for perfect movie viewing. Nick fetched a glass of cranberry juice, her favorite, while Sam helped her get comfortable.

The couch was big and there was plenty of room for the three of them on it. Sam was on her right and she ended up close to him, while Nick sat at the other end of the couch. When the movie started, she insisted on silence.

About a third of the way into the movie, Nick reached down and grabbed her legs, turning Jillian so her feet were in her lap. At first she was confused as he undid her sandals and slipped them off her feet, but then he started a foot massage, which was one of her favorite things in the world. She turned on the couch to get more comfortable, and ended up leaning into Sam. He shifted into a better position and she was practically in his lap, laying back against him. It was sort of a weird position to be in with her stepson, but Nick rubbing her feet felt really good and she was still feeling warm and happy from the mimosas so she just went with it. She didn't even mind when Sam put his arms around her.

Nick had fantastic hands, just like his father. Her worked on her right foot first and seemed to know exactly how to touch her, when to firmly knead her flesh and when to use a light touch. It felt so good that she was playing less and less attention to the movie and concentrating on how relaxed she felt. By the time he moved on to her other foot Jillian felt like she was floating away on a cloud.

At the same time, Sam began massaging her shoulders and neck, sweeping her hair aside so he could work the nape of her neck with his strong, gentle fingers. She was in nirvana. She closed her eyes and settled back against Sam and let the boys' hands work their magic. She easily drifted into that netherworld between sleep and wakefulness. It was almost like a trance where she could feel everything, but her mind was drifting.

"You boys are making me feel so good," she sighed.

Jillian fell deeper into that trancelike state and lost all track of time and space. She was halfway into a dream, a dream stoked on by the powerful feelings the four massaging hands stirred in her body. Without her even realizing it, she'd become very aroused, but body and mind were so disconnected at that point that she did not think about why. It was her stepsons' massaging her that was causing her intense feelings. It was only when Nick's hand was massaging up her leg and just reaching under her skirt that Jillian realized what was happening. And still she did not stop things. She actually parted her legs slightly, reflexively, so his hand could move higher.

With all the moving around, her skirt had ridden up, so that by the time Nick's hand was moving under it he was already caressing her tender inner thighs. At the same time, she noticed Sam was no longer massaging her shoulders, but caressing her neck and her chest, just above her breasts. This is really not a good idea, she thought.

"Boys, what are you doing?" she asked dreamily. She licked her dry lips, but kept her eyes closed.

"Just giving you a Mother's Day massage. It is your special day," Nick said innocently.

"Okay, but be careful. You're getting a bit too personal," she sighed. The horse was already out of the barn on that one. Nick's one hand was already well under her skirt, while his other was caressing her behind the knee, while keeping her legs apart at the same time. Her half-hearted warning did stall his progress, though. Obviously she should jump up and run out of there, but she couldn't make herself do it. All the time she'd been spending alone was really working against her now. Jillian really needed to be touched.

"Don't worry, Jill. We're just trying to relax you and make you feel good," Nick said.

Sam couldn't believe this. He thought Nick was crazy when he started moving his hands up her legs, but after a moment he followed suit and started touching her more intimately too. His heart knew it was wrong, but it was just so damned hot. At first he thought Jillian was asleep and so wouldn't realize what was happening. And he hadn't done anything he couldn't take back. He watched the slow rise and fall of her chest, mesmerized by the swell of her breasts. As they massaged her, her nipples had hardened and now he could clearly seem them through her top, even in the dim light. He so wanted to touch her there and was working his way down when she spoke. He nearly jumped out of his skin and his hands froze in place. But then he saw his brother resume massaging her and he did was well. She didn't seem ready to stop them yet. How far could they get? he wondered.

Nick was wondering the same exact thing. He thought she was sleeping too and when she spoke he thought they jig was up, but she kept laying there and didn't move to stop them. She just warned them to be careful. He'd been through that with girls his own age and usually it meant they wanted him to keep going, but didn't want to appear too easy. He was shocked he'd gotten this far. He could feel the heat from her cunt already and knew she must be really turned on by their massage. There was no way he was going to stop now unless she told him to. His cock was rock hard and he thought there was a chance she might take care of it before the day was over.

Jillian moaned when Nick's fingers grazed her panties with just enough pressure to make her feel it. It was only then that she knew how wet she really was and the fact that she'd soaked through her panties meant that now Nick knew it too. She wanted to be surprised that the boys were going this far, but she wasn't. This was inevitable when she didn't stop them. He nudged her legs further apart and she let him and his fingertips pressed harder into her mound, rubbing in a little circular motion. God help me, I wish my panties weren't there. She gasped and bit her lip, grabbing onto Sam's leg beside her. He finally slipped his hands down and cupped her breasts, kneading them through her top. She loved having them played with and was happy that Sam didn't just tried to maul her. She liked a gentle touch.

Nick pulled her panties aside and slipped a finger inside her. Jillian moaned and instinctively pushed herself at him. Beneath her, she felt a lump in the small of her back and realized it must be Sam's hard-on pressing into her. He was rubbing it against her and she didn't know what she should do. Nick slowly buried his finger inside her and as good as it felt she knew she had to say something. She could not let this go on like it was all okay. She opened her eyes and found Nick staring right at her, like he was studying her every reaction.

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bySexyBeast© 7 comments/ 160762 views/ 107 favorites

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